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
• Article Data: 4

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

Chemical Properties

white to light yellow crystal powde

Uses

Both (+)- and (-)-DIP-chloride are used for asymmetric reduction of prochiral ketones and for the preparation of β-amino alcohols.

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

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

Downstream Products

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

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