112246-73-8

Basic information

• Product Name: (+)-Diisopinocampheyl chloroborane
• Synonyms: (+)-DIP-Chloride,(+)-B-Chlorodiisopinocampheylborane, (+)-Ipc2BCl;(+)-Diisopinocampheylchloroborane, 1.8M solution in hexanes, AcroSeal;(+)-B-Chlorodiisopinocampheylborane((+)-DIP-Chloride);(+)-DiisopinocaMpheylchloroborane in heptanes;Chlorobis((1S,2R,3S,5S)-2,6,6-triMethylbicyclo[3.1.1]heptan-3-yl)borane;B-ChlorodiisopinocaMpheylboran;(+)-DIP-Chloride(TM) 90-105% (approx.);(+)-DiisopinocaMpheylchloroborane, 1.7 M solution in heptane, SpcSeal
• CAS NO: 112246-73-8
• Molecular Formula: C₂₀H₃₄BCl
• Molecular Weight: 320.75
• Product Categories: chiral;Asymmetric Synthesis;B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry
• Mol File: 112246-73-8.mol

Chemical Properties

• Melting Point: 53-55 °C(lit.)
• Boiling Point: 369.6 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: white to light yellow crystal powder
• Density: 0.91
• Vapor Pressure: 2.5E-05mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-Diisopinocampheyl chloroborane(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Diisopinocampheyl chloroborane(112246-73-8)
• EPA Substance Registry System: (+)-Diisopinocampheyl chloroborane(112246-73-8)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 112246-73-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Diisopinocampheyl chloroborane is used as a reagent for the asymmetric reduction of prochiral ketones, which is crucial for the synthesis of various pharmaceutical compounds. This application is significant because it allows for the selective production of specific enantiomers, which can have different biological activities and reduce potential side effects.
Used in Chemical Synthesis:
(+)-Diisopinocampheyl chloroborane is also used for the preparation of β-amino alcohols, which are important building blocks in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and natural products. The ability to produce these compounds with high enantioselectivity using (+)-DIP-chloride makes it a valuable tool in the development of new and improved chemical processes.

InChI:InChI=1/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+

Synthetic route

L-diisopinocampheylborane (21947-87-5) → B-chlorodiisopinocampheylborane (112246-73-8)

Conditions	Yield
With hydrogenchloride In pentane 0°C;;

(-)-α-pinene (7785-26-4) → B-chlorodiisopinocampheylborane (112246-73-8)

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

Pinene (80-56-8, 177698-18-9) → B-chlorodiisopinocampheylborane (112246-73-8)

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

monochloroborane dimethyl sulfide complex (63348-81-2) + (+)-α-pinene (7785-70-8) → B-chlorodiisopinocampheylborane (112246-73-8)

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

B-chlorodiisopinocampheylborane (112246-73-8) + allylmagnesium bromide (1730-25-2) → B-allyldiisopinocampheylborane (106356-53-0)

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℃;

B-chlorodiisopinocampheylborane (112246-73-8) → (1S,2S,3S,5R)-(+)-isopinocampheylamine (13293-47-5)

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

B-chlorodiisopinocampheylborane (112246-73-8) + (S)-3-methyl-4-(triisopropylsiloxy)-butan-2-one (199857-42-6) → C34H63BO2Si (199857-59-5)

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

B-chlorodiisopinocampheylborane (112246-73-8) + 1,3-dilithio-2-methylenepropane*2TMEDA (107901-60-0) → (S,S)-1,3-bis(diisopinocampheylboryl)-2-methylenepropanes (222624-76-2)

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

B-chlorodiisopinocampheylborane (112246-73-8) + (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	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;

B-chlorodiisopinocampheylborane (112246-73-8) + methyl (2R,3S,4R)-3-(t-butyldimethylsilyloxy)-2,4-dimethyl-5-oxohexanoate (261968-06-3) → C35H63BO4Si (303964-39-8)

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

allylmagnesium bromide (2622-05-1) + B-chlorodiisopinocampheylborane (112246-73-8) → B-allyldiisopinocampheylborane (106356-53-0)

Conditions	Yield
In tetrahydrofuran

(4R)-4-(Benzyloxy)pentan-2-one (87841-68-7) + B-chlorodiisopinocampheylborane (112246-73-8) → C32H49BO2 (445423-03-0)

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

B-chlorodiisopinocampheylborane (112246-73-8) + (3R,4R)-(E)-3,5-dimethyl-6-iodo-4-methoxyhex-5-en-2-one (477200-95-6) → C29H48BIO2

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

2-methylallylmagnesium chloride (5674-01-1) + B-chlorodiisopinocampheylborane (112246-73-8) → (+)-β-methallyldiisopinocampheylborane

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

acetone (67-64-1) + B-chlorodiisopinocampheylborane (112246-73-8) → C23H39BO

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

B-chlorodiisopinocampheylborane (112246-73-8) → C34H53BO2

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

B-chlorodiisopinocampheylborane (112246-73-8) → (1R,2R,3S,5R)-2-((E)-(S)-1-Hydroxy-3-phenyl-allyl)-2,6,6-trimethyl-bicyclo[3.1.1]heptan-3-ol

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

1-(4-(Cyclohexylmethoxy)phenyl)ethanone (79615-74-0) + 2,2'-iminobis[ethanol] (111-42-2) + B-chlorodiisopinocampheylborane (112246-73-8) → (R)-1-(4-(Cyclohexylmethoxy)phenyl)-1-ethanol (224445-44-7)

Conditions	Yield
In tetrahydrofuran

2,2'-iminobis[ethanol] (111-42-2) + B-chlorodiisopinocampheylborane (112246-73-8) + tert-butyl 4-oxo-4-(o-tolyl)butanoate (170282-44-7) → t-butyl 4-hydroxy-4-(2-methylphenyl)butanoate

Conditions	Yield
In diethyl ether

2,2'-iminobis[ethanol] (111-42-2) + B-chlorodiisopinocampheylborane (112246-73-8) → (S)-2-Iodo-(2',4'-dichlorophenyl)-1-ethanol

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

benzaldehyde (100-52-7) + B-chlorodiisopinocampheylborane (112246-73-8) → (C6H5CH2O)2BCl

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

1,3-dilithio-2-methylenepropane (53721-69-0) + B-chlorodiisopinocampheylborane (112246-73-8) → (S,S)-1,3-bis(diisopinocampheylboryl)-2-methylenepropanes (222624-76-2)

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

4-trimethylsilyl-3-butyn-2-one (5930-98-3) + acrolein (107-02-8) + B-chlorodiisopinocampheylborane (112246-73-8) → C30H49BO2Si

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;

ethyl 3-butenoate (1617-18-1) + B-chlorodiisopinocampheylborane (112246-73-8) → C26H43BO2

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

B-chlorodiisopinocampheylborane (112246-73-8) → (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	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

B-chlorodiisopinocampheylborane (112246-73-8) → (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	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

B-chlorodiisopinocampheylborane (112246-73-8) → cryptomoscatone E3

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

B-chlorodiisopinocampheylborane (112246-73-8) → C28H42O5Si

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 + B-chlorodiisopinocampheylborane (112246-73-8) → diisopinocampheylborane phosphine-carboxylate ester

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

Upstream product

• 21947-87-5 L-diisopinocampheylborane 
• 7785-26-4 (-)-α-pinene 
• 80-56-8 Pinene 
• 63348-81-2 monochloroborane dimethyl sulfide complex 
• 7785-70-8 (+)-α-pinene 

Downstream Products

• 13293-47-5 (1S,2S,3S,5R)-(+)-isopinocampheylamine 
• 106356-53-0 B-allyldiisopinocampheylborane 
• 445423-03-0 C₃₂H₄₉BO₂ 

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