Home Cart Sign in  
Chemical Structure| 3344-70-5 Chemical Structure| 3344-70-5

Structure of 1,12-Dibromododecane
CAS No.: 3344-70-5

Chemical Structure| 3344-70-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Marshall S. Padilla ; Kaitlin Mrksich ; Yiming Wang ; Rebecca M. Haley ; Jacqueline J. Li ; Emily L. Han , et al.

Abstract: Lipid nanoparticles (LNPs) are the preeminent non-viral drug delivery vehicle for mRNA-based therapies. Immense effort has been placed on optimizing the ionizable lipid (IL) structure, which contains an amine core conjugated to lipid tails, as small molecular adjustments can result in substantial changes in the overall efficacy of the resulting LNPs. However, despite some advancements, a major barrier for LNP delivery is endosomal escape. Here, we develop a platform for synthesizing a class of branched ILs that improve endosomal escape. These compounds incorporate terminally branched groups that increase hepatic mRNA and ribonucleoprotein complex delivery and gene editing efficiency as well as T cell transfection compared to non-branched lipids. Through an array of complementary experiments, we determine that our lipid architecture induces greater endosomal penetration and disruption. This work provides a scheme to generate a class of ILs for both mRNA and protein delivery.

Purchased from AmBeed: ;

Alternative Products

Product Details of [ 3344-70-5 ]

CAS No. :3344-70-5
Formula : C12H24Br2
M.W : 328.13
SMILES Code : BrCCCCCCCCCCCCBr
MDL No. :MFCD00000226
InChI Key :ZJJATABWMGVVRZ-UHFFFAOYSA-N
Pubchem ID :18766

Safety of [ 3344-70-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 3344-70-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 11
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 75.54
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.04
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

6.91
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

5.68
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

5.28
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

5.66
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.51

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.5
Solubility 0.00103 mg/ml ; 0.00000315 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.72
Solubility 0.0000623 mg/ml ; 0.00000019 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-6.42
Solubility 0.000126 mg/ml ; 0.000000384 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-3.4 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.76

Application In Synthesis of [ 3344-70-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3344-70-5 ]

[ 3344-70-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 3344-70-5 ]
  • [ 117-78-2 ]
  • 9,10-Dioxo-9,10-dihydro-anthracene-2-carboxylic acid 12-bromo-dodecyl ester [ No CAS ]
  • 2
  • [ 1802-20-6 ]
  • [ 3344-70-5 ]
  • 1,12-bis(3'-pentylpyridinium)dodecane dichloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% 1,12-Dibromododecane (0.20 g, 0.61 mmol) was dissolved in 4-methyl-2- pentanone (2.0 ml) and <strong>[1802-20-6]3-pentylpyridine</strong> (0.20 g, 1.34 mmol) was added. The mixture was 5 stirred at reflux for 20 h under a nitrogen atmosphere, and the solvent was removed under reduced pressure. The crude was triturated with Et2O (8 x 10 ml), and the solvent was removed under reduced pressure. The residue was purified by Al2O3 chromatography <n="32"/>(neutral, activity H-III)5 using gradient elution (starting with CHCl3/MeOH = 2 % to 10 %). The residue was passed down a column of Lewatit MP-64 anion resin (Cl"), eluting with EtOH. The resulting fractions were combined and the solvent removed under reduced pressure to give the above compound as a light yellow waxy oil (0.28 g, 85 %).5 1H NMR (300 MHz, CDCl3): delta 9.55 (4H, m, CH(2',6')), 8.20 (2H, d, J= 6.5 Hz, CH(4')), 8.07 (2H3 m, CH(3')), 5.00 (4H5 m5 CH2(I)), 3.10 (4H5 m, CH2(I")), 2.89 (4H5 m, CH2(2"))5 2.06 (4H5 m5 CH2(2))5 1.72 (4H5 m5 CH2(3"))5 1.33 (12H5 m, CH2(354,4")), 1.33 (8H5 m, CH2(5,6)), 0.96 (6H, m, CH3(5")). 13C NMR (300 MHz, CDCl3): 164.2, 144.2, 128.5, 61.2, 35.6, 32.2, 31.4, 29.5, 29.4, 29.1, 26.2, 22.4, 13.3, 1 signal obscured or io overlapping. MS: m/z ESI (positive ion) 233 [M-2C1"]2+ (18 %), 465 [M-2Cl"-H+]+ (10). Found [M-2C1"]2+ 233.2136, [C16H27N]2+ requires 233.2144.
  • 3
  • [ 3344-70-5 ]
  • [ 739-58-2 ]
  • poly(4-(dimethylamino)phenyldiphenylphosphonium-alt-dodecane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In DMF (N,N-dimethyl-formamide); for 168h; 4- (DIMETHYLAMINO) phenyldiphenylphosphine (1.73 mmoles, 0.529 g) and 1,12-dibromododecane (1.73 mmoles, 0.569 g) were dissolved in DMF (1 ml) and shaken for 1 week.
  • 4
  • [ 1802-20-6 ]
  • [ 3344-70-5 ]
  • 2Br(1-)*C32H54N2(2+) [ No CAS ]
  • 5
  • [ 3344-70-5 ]
  • [ 156897-06-2 ]
  • [ 1332505-36-8 ]
  • 6
  • C10H12N5O7PS [ No CAS ]
  • [ 3344-70-5 ]
  • [ 19362-77-7 ]
  • guanosine-3',5'-cyclic monophosphate-[8-thio-(dodecanyl)-(4-thio-phenyl-4''-thio-phenylthio)-(dodecanyl)-thio-8]-guanosine-3',5'-cyclic monophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% General procedure: A solution of 8-T-cGMP (200 mM, 1 eq) and N.N-diisopropylethylamine (2 eq) in DMSO was added portionwise over 30 min to a solution of 1 , 12-dibromdodecane (1.5 M, 15 eq) in (0803) DMSO at 40 C. The reaction mixture was stirred until no further reaction progress was observed (< 10 % remaining starting material). The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in (0804) MeCN/water (8:1 , v/v), washed with petroleum ether (3 x) and the aqueous phase evaporated to dryness using a rotary evaporator. The crude product was dissolved in DMF (115 mM). 4,4"-Thiobisbenzenthiol (0.5 eq) and Nu,Nu-diisopropylethylamine (2.2 eq) were added successively. The reaction mixture was stirred until the starting material was completely consumed. The solvent was removed through high vacuum evaporation with a speedvac concentrator. The residue was dissolved in water (1 mL), washed with ethyl acetate (3 x 1 mL), subjected to preparative reversed phase hplc and desalted. (0805) Yield f Purity) :26 % (> 99 %). (0806) HPLC: (57 % MeCN, 30 mM NaH2PO* buffer, pH 6.8). (0807) UV-VIS: Amax = 275 nm (pH 7), epsilon = 24660 (est.). (0808) ESI- S (+): m/z calculated for C56H73N10O14P2S5 (P+H]+): 1337.39, found: 1337. (0809) ESS-MS (-): m/z calculated for C56H77N10O14P2S5 ([M-H] ): 1335.37, found: 1335.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 3344-70-5 ]

Aliphatic Chain Hydrocarbons

Chemical Structure| 693-58-3

A125696 [693-58-3]

1-Bromononane

Similarity: 1.00

Chemical Structure| 4101-68-2

A125763 [4101-68-2]

1,10-Dibromodecane

Similarity: 1.00

Chemical Structure| 112-71-0

A145420 [112-71-0]

1-Bromotetradecane

Similarity: 1.00

Chemical Structure| 111-24-0

A154427 [111-24-0]

1,5-Dibromopentane

Similarity: 1.00

Chemical Structure| 629-03-8

A163362 [629-03-8]

1,6-Dibromohexane

Similarity: 1.00

Bromides

Chemical Structure| 693-58-3

A125696 [693-58-3]

1-Bromononane

Similarity: 1.00

Chemical Structure| 4101-68-2

A125763 [4101-68-2]

1,10-Dibromodecane

Similarity: 1.00

Chemical Structure| 112-71-0

A145420 [112-71-0]

1-Bromotetradecane

Similarity: 1.00

Chemical Structure| 111-24-0

A154427 [111-24-0]

1,5-Dibromopentane

Similarity: 1.00

Chemical Structure| 629-03-8

A163362 [629-03-8]

1,6-Dibromohexane

Similarity: 1.00