(SANITIZED)ORGANOBORON COMPOUNDS. VIII. SYNTHESIS AND PROPERTIES OF DIARYLBORIC ACIDS(SANITIZED)

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP80T00246A005600100002-7
• Release Decision: RIPPUB
• Original Classification: C
• Document Page Count: 8
• Document Creation Date: December 21, 2016
• Document Release Date: January 5, 2009
• Sequence Number: 2
• Publication Date: February 12, 1959
• Content Type: REPORT

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25X1
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(a,:PaY3.a,1 OcKON.3D3. Yilf.
spiv-1;31JD PpoeEaTIS3 et DLNWLDOIO SO138
Mtihallor, 3. 14. aal (avet, Y. A.
la ono of the authors' yrtylokls communication/I,. setbod
of 4iphanylboria acid and its :erivatives has beg& asecribed (1),
of these 4frivatives had the di.ssire to ftrther ssimblisli (Confirm)
,La the literaturdo latapertaising to other diaryloris Said, bar*
authorS to usdertate the synthesie of adaitiosal nolbors of tido
sommlottl.
Thi, following preparations weaS Loadertntea wt % smemss,
4$.1-trompbenyl au& -chlorphonyl boric acids. Isobstyl.seterS
ms1101 Acids vere obtattel ta 40-6:11 of theoretical yield, as sell
esters of the correspondirg omomryl borie arid*, fraa the profte
action of two equivalents of aryl mo..otemiambrceddes with, one *gni
itobwitiborstmo Ttess reactions wsre earrie4 out arid's, cOOditl
eynthesit of isobutyl ester ot ifS'LL'esql bort3 &eii (i)t,
2ArM03,4/1(1-Oes10)* Arr.B(i-ocalle).+ i-"Isgs014(r
rc141.01;er, ;.C1C.64
The eherseteristis IrePertf of these sYmthatoiSed 'store
acids is their stability with xesleect to water had dilute slapril
Their seco64 characteristic is tLeir hinh solubility is olkaliao
ths conS$14mmt formatloa of*alto of dinrylisobotoar brts ao
(M211(GNI - ;s3
? nattsg the wet oolutions of s4eh *alto, cbtained fro&
,
esters of 4isry1bOr1e soils with %Ilevai Alkali metal end alkali' '
reoults Lasepoaificatioa of tc 1xf rouS id the 4A/04 with.
formation of malts of dieryibcris
(AraB(02/-1.-40Cel!si ?'Eso ? (Ara(Q13)ti -CelOag
Thus the barium aalts of Aisryltori3 Solis are easily 010
direct treatment of diarylorie soli with saturated water eolutioll
droxids.
Ta this ut1f, oaame aaioa sapoaification
forms the mat of (gAry1is....1,ut.,cy aoria a'i-i, blt the /reaction yr0
to yr Coluhility of tAri..3 .-Alts of 4it.ey1tcril aci4s.
e eaters of r1;1411e1 an4 ii-p-br*pheml.borie se
easily with aveoull t,i,..1c,a..10'formi,-"..4?aoht...m,sAlts of Correa
sei4e0 rt* estel of 41-;-,"'l2.'-rO;',,t'nY1 h,:rto soli i* im this essil
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it is not aff*cted,bt4c/tootts &count& *Ye* oPoa hotting.,
The diarrlhorie acid salts of the den0r01 forals
[Arsa(c)I)s) Me
af151, ite Ile, At ',4-C1017 p-BreAMO, -clealw
oa a0141ficatioa Aro transformod into vadat
(Arad(011)*) 14. e ?? AragosY ? ita ? me
MO fat/ Of this di naphthyl and di -d -brOMPhis I hod* atidi 0014,
the oorrtapolding diarylborio acids, chile the salt of dl-p-c Voris said
yields is said which correq*nds, fro* aaaltilli to the . to 41, 1114.
chloropheayl bort. said, ii vat alretdy roportei (1) is the 0 it Owl toe,
acid, ,
whets
????
111 contrast to diphenylborlo said, the other diaryl
by the authors, do not fore anhydrides os beating iss vac sou,
ilias IL. fornadupoes loss of ons aryl radical. the, aahrdri
treatment with thloatl chlorlds as 'bora ii at exempla with
aside ,
(4-C100v)a3(011) * 00c1* ---) (0v-Clogi)s* ? a ? a ?
oonclusion it is vial to pause, and oonsider the
the litsraturt, portaiaing to the Ilarylbori0 adds. 2b0 di
via rocently obtained by tatsinger (2) and his co-vorkero
it itfeniaoethyl estor. As to the 41.p-broaapheay1 and the
'torte acids, described by Oafs and scharinhoca (,) aed
casainatica of thslastbods of their preparation as used t
040 to doubt it the above avatimed acid, wort actually oh
ache:latch and later Molnikoff used the, rosotio4 of 09110010e
magnesinabroaldt and trfbutrl borate tor preparatim of the e
Atter working up the, reaction product with &lido mineral tell
the sionoaryl, bort* toil by-products thel residue, under UN.
Dish onataia the unsaponitiol ester ot this diarylborie acid en
it..].'.
tants and Ocharinbeck deterainad the melting point o
said to b? 113,'Cl, vh110 In reality it mat* at 910. The data
*We the 41.p.ch1oropheni1 hest* acid to Ws the following
3(01), 'hilt in realitr its coevoeitiot is (Cleoao)0(010.40.
Pbr.eoyer, Melnikoft, at al erionfoonelp show* that
solervaatittes of p-chIoropbenyl angueslusibronia0 with tr
the 41-0-chlorophon4 boric sold :with t 17% yield together vi
(1S$ of theoretical) of thie no p-chlorophanyl bodes sold.
work, los falai& thtt under the shove stated conditioas oar the
borti sold is obtained A41 0.40 AO ester of 41-1-ch1oroPbspyl
obtainot. '
ii aside, *Wool
tiedaccaarrl bolo
act DO obtatoOd by
aoophthylberia
(A-aloarhe
is, ernedleir is
saphtkyl bort, said
thd teat htitallis"
4-4 eAdAimMAUKI
tkott (4)-timi
00 aathofor load,
. latig oat
opattlties of aryl
gmeaboros conpounds.
and lsolatioa of
tic**, oottld at
not the troll acid
,41-11:bracothaarli
ahlalkoff,
LUCA 6:1414)1
Matto' of et.
borate Ilal4s
a saillect Ada
tiagMelalkott's
-ebloroPh0NY1
?'10 40101.10
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To * 1 soli, ether -benzene eolution of 0.5 40110
broads maintained is the -20 to .10'0 temperature range?
of triisobutyl beret*, dissolved in 50 ml of or ether,
,.machaalcal otttetlea is a period of 11 minutes. (Vas comp
borate ester, the reaatioa tcoperlituri is lowered to tbs -
raw NA the agitatio* of the remotion mass is costinue4
. -Venswadtdar.tba-r40.11.9111;TARcts are treated with 350 ml
The ather.baseens late* is separsted inlif,'tffe 'IVO- solidi
ether. The combined ether -benzene extracts are dried over
The ether-benzene is this removed by distillatiol. Ms
yellowish reside* upon dilution with 50 ad of isopeataae
ail/. The reaction residue was then filtered hod sucked
lova:two soli then dried under norms. field 41.5 gran*
isobutyl este* of di.A.naphthyl hoes acid, malting point
lisation frosts hszems).
1W04. 44 081.20) 6,0 *CV) 6i17 I )47
Cale. for csoa,kao $t 081.22 116.8,5 3 .1?19
Its isopeateae filtrate) attetreneval of the 1
distIlletioa IS osteritied with isobutyl (dead. tea
of 4110obsty1 ester offt-mapthyl bort* said are obtained,
KO aft CM, '
found $1 Ciofr) 115.mi 1,54) 15.60, MT
fog (eloSr),(00age), $1 exc.* 4 .42; DI.76`
The ieobwtyl ester of di....4 -naphtha beris *el.
11A0 subateaces *mill' soluble in 'beaten* sad ehlorofori,
petroleum ether atei methyl alcohol, and insoluble is i
of et -as41011. Berle acid is a colorless liquid. upon set
moisture, it is *sally hydrolysei, liberating the 114 -mug*
1
tropius Salt ?till-A- ohthyl borie aeld.
Tea areas of isohutyl ester of di-.4-aaphihyl he
2G.]. of seth,ft alcohol. 35.1 of .50$ aqueous anemia er*
tice. A *lett **Utica is produced momentarily, et.* ttd,
putstaacs is formed. Atter halt hour agitation, the ern
sucked dry, rube' with methyl alcohol and dried under
tt:
weight. die14, 8.8 gams of the tempauml eat of di -4. -
roProseetisd $7.5 theoretical, 4.0. 101-107'0. After roc
sotkil eloohol, salt moats at 107-108C. '
,
found igs Ciao 71.4*,
011r. for ((c3ol7)0(01)$) PS $1 C1030 0111 all)-17,
The 141001114 salt of di-0.-rmihtbirlboria 401410
000Vouad, lilt, soluble. in beanies and it hot mist191 111
te oeld *ethyl alcohol, and insoluble is rate ft the
4rdrelfeed.with liberetion of moods and naphtbaleni and
? t Armaplothylmagnes Jun'
.221 sole* (3* grow)
added with istsasiv*
Was of Waiting
. to .71'4 temperstere
or ePoriod bre.
of 5,thydroehleria *aid.
ratrestet with-
athydrcee sodiun seltet11.
tug decent slightly
up SP a installs*
carefttly imbed with
6111 of theoretical) of
044?0 (Ott* mrpotal,..
3.44
0 a **darter* or/stet*
slighttr eelmble t*
.0. alsehstfl ester
. Of etsorPboriS
bort* sel&
is mat are nixed with
with hi** *eta.
colones* erystallinet
are filtered lad
until ocostant
tlql harts mil,
sta3.lisatic01 fro*
3.??4, 1.20) it 4.12) 4.09
3. 4.ki.
010c1.008 tall!**
selablit
Itcalits
roe the A .40gohthr4
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bort* Sett.
tri.6k-nakhtliatorie acid.
k.94
area of the emsloollus out of 41.4.43apht,41
is 50 ml of listhylsthmr. To the mixture 3 ml of 62 erfroohl
with iatessiwe snitstioa with the reoultirs raattioa mixture
rod. The ether /Arse is eePoreto4 out, while the wstst layer
With diatlirl *that. The combtromi mthcr astiacts are thescre
remove ether, sifter which the residue is heated to 034 for 1
reactios Product (the resits) Is thee dimsoIwel is minimum
them promipitsted gutty addition of 1021 of isopmetsee.
tii."-mkplatbyl bort. aci4 are obtsinsd, rapresentlat 71.7% of
seltit4 Poise 113-11110'0. After recrystallimation fros petrel
41-A-maptly1 bort* soil was founI to mmlt at 114.5-11$'1.
INgusd Ot e4.85, 84.90) 4 5.26, 5.,41 3.21#
Oils tot de01ls20 $1 d8513 353j 2343
? the 41.0444aphhhrl, boric aoitt is a oolorlefer_ errs
re411.1.17 eoloble iihessants very slishtli soluhle is ether,
to4,,, Ivo* hwoh trolgtepo is vaomme, ehewe solitisipoisto *4
titetaefo *se of the seYetlY1 groups Is split off as maohthal
borts soil; is chtsined.
rls sci4 are mixol
xis soli, ars added
mini sell to Aveloe
Is extrsete4
distille4
-18 istmetee the
laintat of by
1.15 gram OS
theoretical yield,
ether* the pars
0
to gruel of 41 -0`stephtbyl Dori* 6114 are dispel
ohlori40 mitts soletios ralurs4 for 2 hours. Vbe thiemrI
retors4 iS neap*, WI residue is recrystelllx04 fro* that
'mixture, 1.9 gram (98 percent of theoretical yield) of the
"aalthrtrido ere ohteiee4) ealtirn point 190.192'0.
Found Olaf 21.80, 91.96; 2 10.2k
csis." tor (Clogr)aIKCCI,03021 Cioiir 92.28 111 4.3k
This anhydride is acacrledia, crystalline ribstase
soluble is basses* and itsoluble is either petrolous ether or
tedlostr1 *Oatof 414-troeopharri bone soli
S2 a I molar ether solutloa of 0,63 moles of p-h
prepers4 by the method described by Pia (1), 0.25
terstes 41ssolyet is 1004 of sbeoluto ether, are Adotritt
Nritstiosiis the 40 to ,50?43 temperature veto' withie spirt
tto renitis41 resstios **AC it thee &Wore agitate,. tor 0
teoperature tsa? the Mottos products ere thee tree
4tialochtorie Soil. the residue, atter ethot rewrap lies
120)1041. tlotel NA fraotionstest is remain fro. OlerSea
by Utmost, The distillate is obtained as two entOtiCe.,
tolPtresWo LW4i tte setoat is the 138-1010.3 raw, both at
0$001 fertber frsotiogatioe, 38 gram' (39$ Of theoritioel 7140
of 4t-f-troNorbeell borts amid, a.p, 161.163?0 at I MS Agi
theoretical 71,14) of Allsobutyl ester of $-trosopbomyl, hoes
at / el, SO (441 /./.140) 414 obt4144.
140$1 eeleeeitnt
lee of tellsohutyl
tessivesechisioal
of aN0 bat 20mh
is th,
with kto_11 00
et 'Mika, 10, at
is stmeepters of
at IA the 1.01-136io
no se 921110111114
of isdbutit sitar
30 itrols OS 02
lis 16,14 10941000
dl
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. Found $s BrelsR4 i8,73, /0.0; I 2:63, 2.
for 4Th 3(c414) 8ree4R4-0.8* - - ? I 205 ?
/mad $t IWO* 42.72, 49.811 s 3.270 11
Cale. for (hrea14)1004,4 $: BsAlto 119.83 3)./16
The isolmatyl ester of di-p-brumophenyl bogie acid is colorless" very
vlecous 1lcah4 rubstwo that slc,rly "sets" vv.* st,?4?440g at tmapersture.
It iS soluble La most of oremmic **Ismaili and is slimaY deocapo is the ate*
The diisobutyl ester of p-bromopbanyl. bort* *cid is a colorless liquid whist is
vapidly saponified is thi. sir tor:erg p-brasophetail bode sett.
Ammont4 salt of 41-p-bronapheny1borie sett. '
2.2$ v, us of isobutyl ester of ii-p-brommphsall 'bort told ars lased _
with j al of 30, rater splutioa of ammonia. lb* resulting' cry, alit* presipitated
La filtered, sucked dry, washed with rater ant tried ia vacua* stastestt VOSS.
1.85 greas of the tamoniva salt of di-p-brcoophesyl 'bort* said ? dtained
(1.1. 13,1-13,5'0). 1M,11 represents 81.5$ of theoretical, field. Atter riesTstalli,*
sstica from bantam*, the a.p. vas found to be 134.1)r0..
found $t 3resP4 8).421 I 2. 2.92) Ilt* 3.61
We for (OresR40211(02)8) Bre.64 65.23/ ? 2.
The eingsmilor salt of di-p-bromophavatorie said is a colarlesip *Of+
loss, crystalline substance, soluble is eth71 oo4oethr/ alootto * rit-0411
soluble titan:eat ia isopentame
CstdaseLvi salt of 414-broaolhanyl boric sulk
1.21 grams of isobutyl ester of di-p-bassaphisql bort
*arid in the eguivaleat Tomtit, of s rater solution of Potooll
(3,614 of 0.81) meter which the 'star is flails roared under
?
. TWO teeperature raviti La the small sweep of nitroge. The re
*moist* of colorless crystals. Attar recrystallisation fras b
mizture, 0.8 soma of product ars cbtainel.
Pound $1 Breolfg,, 78.58, 710.67) 3 2.71' 2.
Cale for I(Bre0.4)aDOS)2114" $t Brco$4 7e.70. '3 243
Its potsseitus salt of 1.1.-p-bromaptow1 Dori sett ill
rater and alcohol*, insoluble La btneer.e, petrol.mba ttbse ot
treatment with dilute mineral act% the di-p-bAmoplassyl bar'.
guntitatircly.
All-brcasothemyl Dori* &silt.
1.65 gramie of the annonium salt of di-b-brasetkbeevyt
treated with diluted hydrochloric acid. The rematios product is
with ether, after vbiet ether is rewired by viscutus erreporstion.
Admired, it i saall glantity of isopentant. 1.30 gams (86 of
of 4.14-brcompbasyl boric acid, are obtained. Atter recrpe
owe ether, the melting point vas fount to be 9041.'0.
Sett as* lit*
1011rcaddet
it ties 60..
till rvisidad
ans?enstlerad.
I 9.31p 9.ett
181
soluble ia I
teal. tVall
ii is regenerated
?aeld ars'
this esstristed
The resifts is
tbeorrtiml yield)
tits from petrol*
Fount $1 0 42.610 142.69, s2.85, 2.66k 3).18, PAT..% 47.10
ale. for CadaDOBra $ s0 42. hl H2.6/ 33. 18 , 05
?
. ?
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The di-p-brotsoPhen4 borio ail da 'e color/eee crYstalline eu
solublt ix alcobols and is 'benzene, slightly soluble Lap/Aro
is isopesteme. It nal also bo obteited upon eoidificstios o
as maationed previously. 0.889 Srlme of potessitla salt yield
upon acidification with dilute hyirochlorie.
Isobutyl ester of di-p-chloroheiy1 bcrio &eft.
20, 1 molar other solution vt 0.6 moles of P-chlo
irati-airniteitainitt-lartt, -.)50t to Atte.tprkerttor? m404 O.
isobutyl borate, di000lweiJis 100 ml of dry ithet," aro mtiv,
one halt bor with intensive mechanical agitation: the react
further cool*" to .70 to -75'0 ani agitated for a 941104 of a
next day the reaction products ere trested with 450 ml of) P
acid. the residue, lifter removal of ether is estorifiedsdth
alcohol and attor removal of coals alcohol by distillation
(ras the Claysio flask is *stream of dry nitrates.
is obtained its tro separate fro:times Tho 70-140 haat,
1141-16Y0 fraction (at 2 me 4). %Yvon further fractionation
/*col ooluma is I stress of'dry nitrogem )1 gm*. of ikkoetY/
ehloroPheayi, Doris sold aro obtained at 134-136?0 (1
represosts 140 percent of theoretical yield Also 11 grass, of
' p-eh1orepheey1 bone soil ar44 ohtsismt at 93"95.4 (14111M4).
000tiod 25$ of theoretical yield.
iround $:0/0014 72.56, 72.25 15.'3, 5.5
Cal'. for (0,c44)0(oc09) $xc1eer4 72.68 I 1.52
140,44 $0100,4 141.,A, )41.09 3 1.9(4 4.
We. toe (adolso)4(08409)*$:c1c,34 hi. 3.
/sobityl ester of 41 -p-chlorophanyl borie soil ii 0
viscous liquid. It is immiseibl0 Idtb vast, stiOeible with*
solvents. /t 10 rapidly decomposed in the all. The ditiobm
*ADA hoee said is a co/crless, mobile liquid, mIseiblewl
orgasio solvents. It is instantly hydrolyzed is the dr, t
04.1011. 1)ette telt.
Barium salt of 414.ch.lcrophasy1 boric acid.
? ,
1.73 crams of isobutyl eater of di -P-ohlq.?01W/' bc
for $.10 minutes with 19 al of I seturstall solution 01, rOaat
barius hydroxi40. ThO voluaniousk flocculent pritelPitat44, vhf
stouts,' is filtered off, sucked dri, washed with water *offs
waight webs Plcuumt. 1.7 Aram, of dry product are obtained,
putout of theotaticol yield. for dsterminstion orbs:lust kn
prOduct, were heated withskaown anuust of 1 I hydrochlorio sai
is the* titratodivith stattsrt 1 X alkali.
:gm" "St ps 20.21), 20.26, 01064 61.
Cale* for 21044 t(08)alaan St Da 20.t0) dlesge 66.
The bariust salt of 41 -$ -chlorogemfl bort. sail Is 4
lino substancO. The salt is not soluble lentos, brume., i
quite solublo in meth,/ and ethyl alcohols. Act164"of dilute
Yield free di -chlorophonyl bort, acid.
henfl teldnadius
I mole, of krt.* '
tibia-sported' of,
as mixture IS thus
9 hour*. 00 the
? last hydrochlorie
25 ml of isObetyl
14
remittal prodeots
(sk a ale $4) awl the
tit the aid, of
*star of di -P-
1.1414. thig
ischmtyl Mtge' Of
1.00618 ropfc.
is ailid are shaken
atlas) of
Is lovas atter a foe
of to oototoo4
eh roproosato 89.5
weight* of Um
? /b0 *geese said
I 61.91, 20.14,3.09
25.21
ogosloolo. cilstal-
taae, it is
Marie laid
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Di-p-chiorophanyl boric acid.
2.0 grams of the tari,...a salt of 11-9..:chloroPhaA7t
With 10 al of 101 diluted hydrochloric Acid. it. a6nestar1
changes to t colorless crystallite substance, .which 1$ tilt.z
reshot with rotor awl driei over anbydryus calcium chloride.
produsty which melts it 76-78'0, is obtained. Ay U44,1,1111 i
notohydrate of 4.1.p-ch1orophely1 bcric acid. Wavle Ar7iAt
,chlorobeatene ant p-chloropheuyl boric acid.' :
found $1 c54.55, sk.29; 0440, 4.281 k.o8,
Cals. for Cloh~o $i C53.55 12 02
its monohydrate of 11-p-chloroptenyi tor!, aeig, ts
nethil and ethyl alcohol, insoluble ia water.
1*iiiu salt of boric aeit.
2.8k vans of ischutyl ester of di-p-chloropheafX
solve., in aa squints** amouat of sodium hydroxide' OA Ai of
resulting solution is heated to about 60-70'S ant then vats*
distillation under a reduied pressure. The residue in washed
Inlet in vacuun. field 2.2 exams of dri product.
fnulut $1
Cale. tor ClaSiopOsCloltls
Its sotiux salt is
benzin,' patroleunk ether and
Al-p-chlorophsayl:boris sea
r10 said are shaken
fOrnet.senlsios
off, racket 4ry,
1.ias of 447
corrssposste del
oVeses It into
.83 Cl 26.36 26.66
c240
141. tebeassuri
Is r.420 1.56 3 3.'3, 3.6*
s 3.7a
quite soluble is alcohols emirs
isopentans. aeidificaiion #
is obtained.
COACTZOIOSI
rsobutyl *stark, of ii*c(-naPhthfl, 4.1-p'br(4?Vhe*4 8" 41
acid, vets obtainel.
rag shank that the isobutyl esters of tii..04-aaphtkf1,
gi_p_emoropheayl boric acid, upon heating with potassiws
al wsli as upon action of n.mmontuis or barium hydroxides*, f
iag metal salts of ths ab enantivned said,.
3.1 Acidification of the above menti ,..ted astal salts pr....Antes
itli4r0a0Pbanfl ant tt-p-nhlcrophanyl torte acids.
k. Some of tee late, previously reported; ;ortaisias to
p-chlorophaayl boric acids were iphywn Obis erroneous.
LrTERAM
(1) Mikhailow, 11.14. and fairer, f.A., 0.4.1 10.111.),531, 119551.
Skoog, J., Ames, Y. $.AN.Chem.Soe. 7?,4041' (19541. 0) Kdtie
j.preicaeg.1411,133,4950]. (4) Malnikcw, I I Robitskaildf.
(190). (5) Pi1 I., 1.a.cl.Soe.122), i2 hi (6) wittie,4
Adckerb, A., Ailf, A., Ann. gl.? 110-(1949).
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