tert-Butoxy bis(dimethylamino)methane

HCID 79885
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Basic information

CAS
5815-08-7
Standard SMILES
CN(C)C(OC(C)(C)C)N(C)C
InChIKey
HXRAMSFGUAOAJR-UHFFFAOYSA-N
Molecular formula
C9H22N2O
Average molar mass
174.28 g/mol
Monoisotopic mass
174.17321333

Names & identifiers

Preferred name
tert-Butoxy bis(dimethylamino)methane
IUPAC
N,N,N',N'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine
English name
tert-Butoxy bis(dimethylamino)methane
Molecular formula
C9H22N2O
Molecular weight
174.28

Names & synonyms

5815-08-7tert-Butoxy bis(dimethylamino)methaneTert-Butoxybis(Dimethylamino)MethaneBredereck's reagentBREDERECK REAGENTJEJ0U558F7EINECS 227-383-9bis(dimethylamino)-tert-butyloxymethaneUNII-JEJ0U558F7BREDERECK'S REAGENT [MI]DTXSID00206888tert-butoxy-N,N,N',N'-tetramethylmethanediamine
Show more names
T-BUTOXYBIS(DIMETHYLAMINO)METHANE5815/8/7BUTOXYBIS(DIMETHYLAMINO)METHANEtert-Butoxy bis(dimethylamino)methane technicalBredereck'sreagenBREDERECKS REAGENT
1-tert-Butoxy-N,N,N',N'-tetramethylmethylenediamine1-(1,1-DIMETHYLETHOXY)-N,N,N',N'-TETRAMETHYLMETHANEDIAMINERefChem:188169DTXCID301293791-tert-butoxy-n,n,n',n'-tetramethylmethanediamine[(tert-butoxy)(dimethylamino)methyl]dimethylamineMFCD00042858N,N,N',N'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine

Database identifiers

CAS
5815-08-7
PubChem CID
79885
DTXSID
DTXSID00206888
UNII
JEJ0U558F7
EC Number
227-383-9
Nikkaji
J218.073A

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
15.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
12

Physicochemical properties

Boiling point
50 · 50-55 °C/15 mmHg (lit.)
Density
0.844 g/mL · 0.844 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.422(lit.)
Flash point
106 °F · 106 °F
storage temp.
-20 °C · Sealed in dry,Store in freezer, under -20°C
solubility
Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 65 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationMethanediamine, 1-(1,1-dimethylethoxy)-N,N,N',N'-tetramethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesFlam. Liq. 3 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (100%)

Regulatory information

Regulatory InformationMethanediamine, 1-(1,1-dimethylethoxy)-N,N,N',N'-tetramethyl-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
ridadr
UN 1993 3/PG 3
hs_code
29221990
risk_code
10-36/37/38

Chemistry & industry

Applications · 4 items

DescriptionBredereck's reagent, chemically known as tert-Butoxy bis(dimethylamino)methane, is a versatile reagent. It can be used for a-methylation, a-methylenation, and a-amidation of multiple carbonyl systems or compounds with active CH groups. The advantage is the in situ generation of strongly basic alkanes (t-BuO-) and the generation of the corresponding iminium ions by thermal decomposition. After the Mannich reaction of the carbonyl substrate with the in situ generated iminium ion, the dimethylamine is eliminated from the adduct B- in the final step to give the condensation product, which can be converted into various types of compounds.

UsesReactant for:• ;Preparation of pyrroloquinazolines as photochemotherapeutic agents1• ;Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition2• ;Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction3• ;Aminomethylenation reactions4

UsesReactant for:Preparation of pyrroloquinazolines as photochemotherapeutic agentsEnanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical additionSynthesis of camptothecin via intramolecular isomuenchnone cycloaddition reactionAminomethylenation reactions

UsesMild enamination reagent; catalyst in ring-opening polymerization reactions.

Upstream & downstream products

Suppliers100 total

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
普善实业（陕西）有限公司029-81310890 18165209495 · [email protected]

Related reactions

341 records
New reaction record

Compound notes

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