(+)-Diisopinocampheyl chloroborane supplier

Name
(+)-Diisopinocampheyl chloroborane
EINECS
CAS No. 112246-73-8
Article Data4
CAS DataBase
Density 0.99 g/cm³
Solubility
Melting Point 53-55 °C(lit.)
Formula C₂₀H₃₄BCl
Boiling Point 369.6 °C at 760 mmHg
Molecular Weight 320.754
Flash Point 177.3 °C
Transport Information UN 3261 8/PG 2
Appearance white to light yellow crystal powder
Safety 26-36/37/39-45
Risk Codes 34-37
Molecular Structure
Hazard Symbols C
Synonyms Borane,chlorobis(2,6,6-trimethylbicyclo[3.1.1]hept-3-yl)-, [1S-[1a,2b,3a(1R*,2S*,3R*,5R*),5a]]-;(+)-B-Chlorodiisopinocampheylborane;(+)-Chlorodiisopinocampheylborane;(+)-DIP-Cl;(+)-DIP-chloride;Borane,chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]-;
PSA 0.00000
LogP 6.36130

Synthetic route

: 21947-87-5
L-diisopinocampheylborane

: 112246-73-8
B-chlorodiisopinocampheylborane

Conditions

Conditions	Yield
With hydrogenchloride In pentane 0°C;;

: 7785-26-4
(-)-α-pinene

: 112246-73-8
B-chlorodiisopinocampheylborane

Conditions

Conditions	Yield
With monochloroborane dimethyl sulfide complex In hexanes at 20 - 30℃; for 2.56667h; Cooling with ice; Inert atmosphere;

: 80-56-8, 177698-18-9
Pinene

: 112246-73-8
B-chlorodiisopinocampheylborane

Conditions

Conditions	Yield
With monochloroborane dimethyl sulfide complex In tetrahydrofuran at -10 - 20℃; Inert atmosphere;

: 63348-81-2
monochloroborane dimethyl sulfide complex

: 7785-70-8
(+)-α-pinene

: 112246-73-8
B-chlorodiisopinocampheylborane

Conditions

Conditions	Yield
In hexane at 30℃; for 3.16667h; Cooling with ice; Inert atmosphere;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 1730-25-2
allylmagnesium bromide

: 106356-53-0
B-allyldiisopinocampheylborane

Conditions

Conditions	Yield
In diethyl ether at 0 - 20℃; for 1h;	96%
In diethyl ether at 20℃; for 1h;	96%
In diethyl ether at -78 - 23℃;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 13293-47-5
(1S,2S,3S,5R)-(+)-isopinocampheylamine

Conditions

Conditions	Yield
With hydrogenchloride; methanol; sodium hydroxide; trimethylaluminum; hydroxylamine-O-sulfonic acid Yield given. Multistep reaction;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 199857-42-6
(S)-3-methyl-4-(triisopropylsiloxy)-butan-2-one

: 199857-59-5
C34H63BO2Si

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0℃; for 0.5h;
With triethylamine In diethyl ether at -78 - 0℃;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 107901-60-0
1,3-dilithio-2-methylenepropane*2TMEDA

: 222624-76-2
(S,S)-1,3-bis(diisopinocampheylboryl)-2-methylenepropanes

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 3h; Substitution;

: 112246-73-8
B-chlorodiisopinocampheylborane

(CO)5Mo=C(OLi)[(E)-PhCH=CH]: (CO)5Mo=C(OLi)[(E)-PhCH=CH]

: (1R,2S,3S,6S,8S)-2,9,9-Trimethyl-3-((E)-styryl)-5-((1S,2R,3S,5S)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.02,6]decane

Conditions

Conditions	Yield
Stage #1: B-chlorodiisopinocampheylborane; (CO)5Mo=C(OLi)[(E)-PhCH=CH] In diethyl ether at -78℃; Substitution; Stage #2: In diethyl ether at -78 - 20℃; Cyclization;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 261968-06-3
methyl (2R,3S,4R)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-5-oxohexanoate

: 303964-39-8
C35H63BO4Si

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0℃; for 1h; Condensation;
With triethylamine In diethyl ether at 0℃; for 1h;

: 2622-05-1
allylmagnesium bromide

: 112246-73-8
B-chlorodiisopinocampheylborane

: 106356-53-0
B-allyldiisopinocampheylborane

Conditions

Conditions	Yield
In tetrahydrofuran

: 87841-68-7
(4R)-4-(Benzyloxy)pentan-2-one

: 112246-73-8
B-chlorodiisopinocampheylborane

: 445423-03-0
C32H49BO2

Conditions

Conditions	Yield
With triethylamine In diethyl ether at -78 - 0℃; for 1h;
With triethylamine In diethyl ether at 0℃; for 1h;

: 112246-73-8
B-chlorodiisopinocampheylborane

: 477200-95-6
(3R,4R)-(E)-3,5-dimethyl-6-iodo-4-methoxyhex-5-en-2-one

: C29H48BIO2

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0℃; for 3h;

: 5674-01-1
2-methylallylmagnesium chloride

: 112246-73-8
B-chlorodiisopinocampheylborane

: (+)-β-methallyldiisopinocampheylborane

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;

: 67-64-1
acetone

: 112246-73-8
B-chlorodiisopinocampheylborane

: C23H39BO

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 0℃; for 0.75h;

: 112246-73-8
B-chlorodiisopinocampheylborane

: C34H53BO2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / -78 - 23 °C 2: tetrahydrofuran / 2 h / -90 °C View Scheme

: 112246-73-8
B-chlorodiisopinocampheylborane

: (1R,2R,3S,5R)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptan-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diethyl ether / -78 °C 1.2: diethyl ether / -78 - 20 °C 2.1: H2O2; NaOH View Scheme

: 79615-74-0
1-(4-(Cyclohexylmethoxy)phenyl)ethanone

: 111-42-2
2,2'-iminobis[ethanol]

: 112246-73-8
B-chlorodiisopinocampheylborane

: 224445-44-7
(R)-1-(4-(Cyclohexylmethoxy)phenyl)-1-ethanol

Conditions

Conditions	Yield
In tetrahydrofuran

...Expand

: 111-42-2
2,2'-iminobis[ethanol]

: 112246-73-8
B-chlorodiisopinocampheylborane

: 170282-44-7
tert-butyl 4-oxo-4-(o-tolyl)butanoate

: t-butyl 4-hydroxy-4-(2-methylphenyl)butanoate

Conditions

Conditions	Yield
In diethyl ether

...Expand

: 111-42-2
2,2'-iminobis[ethanol]

: 112246-73-8
B-chlorodiisopinocampheylborane

: (S)-2-Iodo-(2',4'-dichlorophenyl)-1-ethanol

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water; 2,2',4'-trichloroacetophenone

: 100-52-7
benzaldehyde

: 112246-73-8
B-chlorodiisopinocampheylborane

: (C6H5CH2O)2BCl

Conditions

Conditions	Yield
In tetrahydrofuran Kinetics; byproducts: α-pinene; N2 atmosphere, 25°C;

: 53721-69-0
1,3-dilithio-2-methylenepropane

: 112246-73-8
B-chlorodiisopinocampheylborane

: 222624-76-2
(S,S)-1,3-bis(diisopinocampheylboryl)-2-methylenepropanes

Conditions

Conditions	Yield
In diethyl ether treatment of di-Li-compound suspension with 2 equiv. borane;

: 5930-98-3
4-trimethylsilyl-3-butyn-2-one

: 107-02-8
acrolein

: 112246-73-8
B-chlorodiisopinocampheylborane

: C30H49BO2Si

Conditions

Conditions	Yield
Stage #1: 4-trimethylsilyl-3-butyn-2-one; B-chlorodiisopinocampheylborane With triethylamine In tetrahydrofuran at -5 - 0℃; for 2h; Inert atmosphere; Stage #2: acrolein In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; enantioselective reaction;

...Expand

: 1617-18-1
ethyl 3-butenoate

: 112246-73-8
B-chlorodiisopinocampheylborane

: C26H43BO2

Conditions

Conditions	Yield
With triethylamine In (2)H8-toluene at 0℃; for 0.166667h; Inert atmosphere;

: 112246-73-8
B-chlorodiisopinocampheylborane

: (4R,6S)-6-((tert-butyldimethylsilyl)oxy)-7-((4S,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)hept-1-en-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 4 h / -78 - 20 °C 2.1: tetrahydrofuran / 1 h / -78 °C 2.2: NaBO3·4H2O / 1.5 h / -78 - 20 °C View Scheme

: 112246-73-8
B-chlorodiisopinocampheylborane

: (4R,6R)-6-((tert-butyldimethylsilyl)oxy)-7-((4S,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)hept-1-en-4-yl acrylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 4 h / -78 - 20 °C 2.1: tetrahydrofuran / 1 h / -78 °C 2.2: NaBO3·4H2O / 1.5 h / -78 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 3.2: 2 h / 0 °C View Scheme

: 112246-73-8
B-chlorodiisopinocampheylborane

: cryptomoscatone E3

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 4 h / -78 - 20 °C 2.1: tetrahydrofuran / 1 h / -78 °C 2.2: NaBO3·4H2O / 1.5 h / -78 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 3.2: 2 h / 0 °C 4.1: Grubbs catalyst first generation / dichloromethane / 4 h / 40 °C 5.1: hydrogenchloride / water; tetrahydrofuran / 2 h / 0 - 20 °C View Scheme

: 112246-73-8
B-chlorodiisopinocampheylborane

: C28H42O5Si

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 4 h / -78 - 20 °C 2.1: tetrahydrofuran / 1 h / -78 °C 2.2: NaBO3·4H2O / 1.5 h / -78 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C 3.2: 2 h / 0 °C 4.1: Grubbs catalyst first generation / dichloromethane / 4 h / 40 °C View Scheme

: sodium phosphine carboxylate

: 112246-73-8
B-chlorodiisopinocampheylborane

: diisopinocampheylborane phosphine-carboxylate ester

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;

(+)-Diisopinocampheyl chloroborane Specification

The (+)-Diisopinocampheyl chloroborane with CAS registry number of 112246-73-8 is also known as (+)-B-Chlorodiisopinocampheylborane. The IUPAC name is Chloro-bis[(1R,3S,4R,5R)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane. It belongs to product categories of Chiral; Asymmetric Synthesis; B (Classes of Boron Compounds); Boranes; Reduction; Synthetic Organic Chemistry. In addition, the formula is C₂₀H₃₄BCl and the molecular weight is 320.75. This chemical is a white to light yellow crystal powder and should be sealed in cool, dry place without air and water.

Physical properties about (+)-Diisopinocampheyl chloroborane are: (1)ACD/LogP: 7.84; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.844; (4)ACD/LogD (pH 7.4): 7.844; (5)ACD/BCF (pH 5.5): 538852.75; (6)ACD/BCF (pH 7.4): 538852.75; (7)ACD/KOC (pH 5.5): 440715.063; (8)ACD/KOC (pH 7.4): 440715.063 ; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.501; (11)Molar Refractivity: 94.621 cm³; (12)Molar Volume: 321.357 cm³; (13)Surface Tension: 31.697 dyne/cm; (14)Density: 0.998 g/cm³; (15)Flash Point: 177.327 °C; (16)Enthalpy of Vaporization: 59.217 kJ/mol; (17)Boiling Point: 369.598 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25 °C.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to respiratory system and it can cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: B(C1CC2CC(C1C)C2(C)C)(C3CC4CC(C3C)C4(C)C)Cl
2. Isomeric SMILES: B([C@H]1C[C@@H]2C[C@H]([C@@H]1C)C2(C)C)([C@H]3C[C@@H]4C[C@H]([C@@H]3C)C4(C)C)Cl
3. InChI: InChI=1S/C20H34BCl/c1-11-15-7-13(19(15,3)4)9-17(11)21(22)18-10-14-8-16(12(18)2)20(14,5)6/h11-18H,7-10H2,1-6H3/t11-,12-,13-,14-,15+,16+,17-,18-/m0/s1
4. InChIKey: PSEHHVRCDVOTID-YYNWCRCSSA-NC₂₀H₃₄BCl

Product Name

(+)-Diisopinocampheyl chloroborane

Synthetic route

(+)-Diisopinocampheyl chloroborane Specification

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